FAQs

Strategic Fit & Differentiation
Why is this better than our existing sales playbook?

Most teams don't have a separate enterprise playbook, they have a scaled-up SMB playbook built around standardization for the business, not enablement for the buyer. It focuses on what sellers should do during calls, but complex deals hinge on what buyers do between calls (building consensus, justifying investment, aligning stakeholders). If your deals are stalling after demos or dying in "no decision" limbo, your playbook is likely optimized for the wrong part of the buyer journey. We build frameworks that help champions sell internally when you're not in the room.

We've already invested in [MEDDIC/Command of the Message/Challenger]. How does this work with what we already have?

Most teams don't have a separate enterprise playbook, they have a scaled-up SMB playbook built around standardization for the business, not enablement for the buyer. It focuses on what sellers should do during calls, but complex deals hinge on what buyers do between calls (building consensus, justifying investment, aligning stakeholders). If your deals are stalling after demos or dying in "no decision" limbo, your playbook is likely optimized for the wrong part of the buyer journey. We build frameworks that help champions sell internally when you're not in the room.

You talk a lot about enterprise. Can I use this for my mid-market sellers as well?

Absolutely. The deciding factor isn't company size, it's deal complexity. If you're selling deals around $40k+ with multiple stakeholders involved in the decision, these frameworks work. Some mid-market teams operate like SMB (single buyer, quick decisions). Others operate like enterprise (committee decisions, longer cycles). If your mid-market deals require champions to build consensus across finance, operations, and leadership, this applies.

Results & Impact
How do you measure whether this is working?

We work with your team to build out leading and lagging indicators you'll focus on, but all programs center on three core metrics: which deals have a business case attached, the AI quality score of that business case, and how that score relates to deal progression velocity. We also track leading indicators like "no decision" loss rate, engaged contacts per opportunity, and executive engagement depth. During the sprint, we'll align on which metrics matter most for your team and build simple tracking into your existing tools.

How quickly will we see impact on deal progression?

The frameworks go operational immediately after the sprint. You'll usually start seeing impact within 3-6 weeks of running the operating rhythm. Even if you have 6-month deal cycles, deals often sit in one stage for weeks at a time—and we can start cutting that down pretty significantly. Most teams see measurable changes in deal progression within 4-6 weeks across the board, regardless of overall cycle length. The AI scoring system gives managers leading indicators even earlier—they can see narrative quality improving in real-time before deals close. Ultimately, it still depends on how consistent you are with your coaching cadence. I'll be there to support via Slack every step of the way.

What results should I expect to see from this sprint?

I don't make promises about specific outcomes because every team's starting point is different. What I can share is what past clients have reported: deals that previously stalled after demos getting to legal stage in the first 3 months, "no decision" losses being cut in half, and managers that had objective data to coach on narrative quality instead of just activity. One sales manager told me enterprise deals that used to disappear after the first call were moving forward with the steps we put in place.

Implementation & Risk Management
What if our buyers or sales process change after the sprint?

We provide step-by-step guidance and AI prompts to help you update your buyer decision canvas quarterly using your own data. Since all coaching frameworks flow from this canvas, updating it keeps your entire system current with your evolving buyers and process. Most teams review and refresh once per quarter, which takes 2-3 hours and can be done async.

Will this pull my reps away from active selling during critical quarters?

The sprint itself doesn't need to involve reps, only leadership. After the sprint, skill-building sessions happen regardless of which activation option you choose, but they're designed differently than traditional training. These are peer-led sessions (facilitated by managers or enablement, not lecture-based coaching) where reps work on live deals together. Think of it as protected time baked into your week for strategic work on key deals, not theoretical exercises. Every session involves active work on real opportunities, so you're not pulling reps away from selling, you're giving them designated time to do the strategic work that actually moves deals forward.

What's the time commitment required from my team?

During the sprint: 4 collaborative workshops (4.75 hours total) plus 1 internal alignment meeting. The core team (3-4 people: enablement leader, sales manager, potentially RevOps) should commit to attending all workshops. After the sprint: Choose train-the-trainer (2 sales leader sessions, 45 min each) or done-for-you coaching (5 skill-building sessions, 60 min each, plus 1 deal review showcase). All frameworks are built for you, no homework beyond the live workshops and one internal decision meeting.

Who should I bring from our team?

We recommend 3-5 people max for the planning workshops: usually it’s your enablement leader, at least one frontline sales leader, a second-line sales leader and occasionally a RevOps lead, Product Marketing Manager, or Head of Sales. At times teams will include one of their top sellers to include insights from the field as well. The key is involving people who understand your buyers well, and core participants should commit to attending all workshops.

Adoption & Long-Term Sustainability
What happens after the sprint ends? Can we sustain this without you?

Yes. That's the design goal. You'll have complete frameworks, manager playbooks with session scripts, AI scoring rubrics, and implementation guides. The train-the-trainer option (included in base sprint) specifically prepares your team to run this independently. I provide 12 weeks of Slack support to answer questions as you activate, but the system is built for you to own and operate long-term.

Do my managers need to be expert coaches for this to work?

No. The system is designed for real-world sales leaders and enablement leads who have 8-12 other priorities competing for their time. The AI scoring provides objective feedback on narrative quality, so leaders don't need to sit through hours of Gong calls. The coaching cadence gives them specific questions to ask in existing 1:1s and deal reviews. We're not asking them to become writing coaches, we're giving them a system that makes coaching easier and more effective.

Can we update the frameworks ourselves as our product evolves?

Absolutely. All frameworks are delivered in editable formats (Google Docs, Notion, or your preferred tool). The buyer decision canvas includes step-by-step instructions for refreshing it using your own pipeline data and call recordings. The AI scoring prompts can be updated in whatever AI tool you're using (ChatGPT, Claude, or integrated into your existing systems). You own everything we build together.

What if my team doesn't adopt the new approach?

Ultimately adoption depends on how consistent your team is with the coaching cadence. We work together to design a cadence that sellers and leaders can commit to and sustain. However, if your reps and leaders are showing up for key sessions and still struggle with adopting the new process, ping me on Slack and we’ll course correct in real time. My approach focuses on environmental factors rather than individual behaviors, which research shows has 3× more impact on performance. Instead of trying to force new seller habits, I design systems that remove friction and make the new approach the path of least resistance.

Practical Logistics
Do we need Gong/Chorus or other conversation intelligence tools?

No, but they help. Conversation intelligence tools provide richer data for identifying buyer decision patterns during the pre-work phase. If you don't have them, we can build effective buyer-focused systems using CRM analytics, stakeholder interviews, win/loss analysis, and deal outcome data. The frameworks work the same way, we just use different inputs to customize them.

Do you work with remote/distributed teams?

Absolutely. The majority of teams I work with are remote or distributed. All workshops are conducted virtually, and the feedback systems we build are designed for distributed teams. I only work with teams in-person during company SKOs or similar events.

What size teams do you work with best?

I work with sales teams of all sizes, though pricing varies based on team size and complexity. The frameworks scale from small teams (5-10 sellers) to enterprise organizations (100+ sellers). Early stage teams benefit from getting this right from the start. Growth stage teams use it to create consistency as they scale. Enterprise teams use it to align multiple sales segments around common buyer patterns.

Do you personally deliver all coaching sessions, or do you use contractors?

I personally facilitate all coaching sessions while we're in our current phase of direct delivery and framework optimization. This ensures the highest quality outcomes and allows us to continuously improve our methodology. As we scale, I may bring in trained partners, but for now, you're working directly with me throughout the sprint.